JP2016506922A5 - - Google Patents

Download PDF

Info

Publication number
JP2016506922A5
JP2016506922A5 JP2015554245A JP2015554245A JP2016506922A5 JP 2016506922 A5 JP2016506922 A5 JP 2016506922A5 JP 2015554245 A JP2015554245 A JP 2015554245A JP 2015554245 A JP2015554245 A JP 2015554245A JP 2016506922 A5 JP2016506922 A5 JP 2016506922A5
Authority
JP
Japan
Prior art keywords
dimethyl
oxazino
spiro
quinoline
pyrimidine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP2015554245A
Other languages
Japanese (ja)
Other versions
JP2016506922A (en
JP6285960B2 (en
Filing date
Publication date
Application filed filed Critical
Priority claimed from PCT/GB2014/050164 external-priority patent/WO2014114929A1/en
Publication of JP2016506922A publication Critical patent/JP2016506922A/en
Publication of JP2016506922A5 publication Critical patent/JP2016506922A5/ja
Application granted granted Critical
Publication of JP6285960B2 publication Critical patent/JP6285960B2/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Claims (13)

化合物が式（Ｉ）：
Figure 2016506922
 の構造を有する化合物またはその薬学的に許容できる塩であって、
式中、
Ｘはフッ素または塩素であり；
Ｒ１は水素、フェニル、‐Ｃ≡Ｎ、テトラヒドロピラニル、Ｎ‐メチル‐１，２，４‐トリアゾリル、ピリミジニル、ピリジニル、ピラジニル、シクロプロピル、‐Ｃ≡ＣＨ、‐ＣＨ＝ＣＨ２及びＣ１‐Ｃ３アルキルから成る群より選択され、Ｃ１‐Ｃ３アルキルは任意に１つ以上の‐ＯＲ１０、ハロゲン、‐Ｃ≡Ｎ、‐Ｎ３、‐ＳＯ２ＣＨ３、‐ＳＣＨ３、‐ＣＨ＝ＣＨ２、‐ＣＨ＝ＮＯＲ１１及びフェニルで置換されており；
Ｒ２は水素、‐Ｃ≡Ｎ、ピリジニル、Ｃ１‐Ｃ３アルキルから成る群より選択され、Ｃ１‐Ｃ３アルキルは任意に１つ以上のハロゲン、‐ＯＲ２０及びＣＨ＝ＮＯＲ２１で置換されており；
Ｒ３は水素またはＣ１‐Ｃ３アルキルであり；
Ｒ１０はそれぞれ独立して水素、Ｃ１‐Ｃ４アルキル及び（ＣＨ２）２ＯＣＨ３から成る群より選択され；ならびに
Ｒ１１、Ｒ２０及びＲ２１はそれぞれ独立して水素またはＣ１‐Ｃ４アルキルである
前記化合物またはその薬学的に許容できる塩。 The compound is of formula (I):
Figure 2016506922
 Or a pharmaceutically acceptable salt thereof,
Where
X is fluorine or chlorine;
R 1 is hydrogen, phenyl, —C≡N, tetrahydropyranyl, N-methyl-1,2,4-triazolyl, pyrimidinyl, pyridinyl, pyrazinyl, cyclopropyl, —C≡CH, —CH═CH 2 and C 1 -C 3 is selected from the group consisting of alkyl, C 1 -C 3 alkyl is one or more -OR 10 optionally halogen, -C≡N, -N 3, -SO 2 CH 3, -SCH 3, - Substituted with CH═CH 2 , —CH═NOR 11 and phenyl;
R 2 is selected from the group consisting of hydrogen, —C≡N, pyridinyl, C 1 -C 3 alkyl, wherein C 1 -C 3 alkyl is optionally substituted with one or more halogens, —OR 20 and CH═NOR 21 Has been;
R 3 is hydrogen or C 1 -C 3 alkyl;
R 10 is independently selected from the group consisting of hydrogen, C 1 -C 4 alkyl and (CH 2 ) 2 OCH 3 ; and R 11 , R 20 and R 21 are each independently hydrogen or C 1 -C The compound or a pharmaceutically acceptable salt thereof which is 4 alkyl. Ｒ１０が水素、メチル、エチルまたは‐（ＣＨ２）２ＯＣＨ３である請求項１記載の化合物またはその薬学的に許容できる塩。 The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R 10 is hydrogen, methyl, ethyl, or-(CH 2 ) 2 OCH 3 . Ｒ１１が水素またはメチルである請求項１または２に記載の化合物またはその薬学的に許容できる塩。 The compound according to claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein R 11 is hydrogen or methyl. Ｒ２０が水素、メチルまたはエチルである請求項１〜３のいずれか１項に記載の化合物またはその薬学的に許容できる塩。 The compound according to any one of claims 1 to 3, or a pharmaceutically acceptable salt thereof, wherein R 20 is hydrogen, methyl or ethyl. Ｒ２１が水素またはメチルである請求項１〜４のいずれか１項に記載の化合物またはその薬学的に許容できる塩。 R <21> is hydrogen or methyl, The compound or its pharmaceutically acceptable salt of any one of Claims 1-4. Ｒ１が水素、メチル、エチル、フェニル、‐ＣＨ２‐フェニル、‐ＣＨ２Ｆ、‐ＣＨ２ＯＣＨ３、‐ＣＨ２ＣＨ＝ＣＨ２、テトラヒドロピラニル、-（ＣＨ２）３ＯＨ、‐（ＣＨ２）３Ｆ、‐（ＣＨ２）３ＯＨ、‐（ＣＨ２）３Ｆ、‐ＣＨ＝ＣＨ２、‐Ｃ≡Ｎ、‐ＣＨ＝ＮＯＣＨ３、‐ＣＨ２ＳＣＨ３、‐ＣＨ２ＳＯ２ＣＨ３、‐ＣＨ２Ｎ３、‐ＣＨ２ＯＣＨ２ＣＨ３、‐ＣＨ２Ｏ（ＣＨ２）２ＯＣＨ３、シクロプロピル、ピリジニル、‐ＣＨ（ＣＨ３）ＯＣＨ３、ピリミジニル、ピラジニル、‐Ｃ≡ＣＨ、Ｎ‐メチル‐１，２，４‐トリアゾリル、‐ＣＨ（ＯＨ）ＣＨ３、‐ＣＨ＝ＮＯＨ及びＣＨ２ＯＨから成る群より選択される請求項１〜５のいずれか１項に記載の化合物またはその薬学的に許容できる塩。 R 1 is hydrogen, methyl, ethyl, phenyl, —CH 2 -phenyl, —CH 2 F, —CH 2 OCH 3 , —CH 2 CH═CH 2 , tetrahydropyranyl, — (CH 2 ) 3 OH, — ( CH 2 ) 3 F, — (CH 2 ) 3 OH, — (CH 2 ) 3 F, —CH═CH 2 , —C≡N, —CH═NOCH 3, —CH 2 SCH 3 , —CH 2 SO 2 CH 3 , —CH 2 N 3 , —CH 2 OCH 2 CH 3 , —CH 2 O (CH 2 ) 2 OCH 3 , cyclopropyl, pyridinyl, —CH (CH 3 ) OCH 3 , pyrimidinyl, pyrazinyl, —C≡ CH, N-methyl-1,2,4-triazolyl, -CH (OH) CH 3, according to claim 1 which is selected from the group consisting of -CH = NOH and CH 2 OH Compound or its pharmacy Acceptable salt. Ｒ２が水素、メチル、エチル、‐ＣＨ２Ｆ、‐ＣＨ２ＯＣＨ３、‐ＣＨ２ＯＨ、‐ＣＨ＝ＮＯＨ、ピリジニル、‐Ｃ≡Ｎ及びＣＨ＝ＮＨＯＣＨ３から成る群より選択される請求項１〜６のいずれか１項に記載の化合物またはその薬学的に許容できる塩。 A claim wherein R 2 is selected from the group consisting of hydrogen, methyl, ethyl, -CH 2 F, -CH 2 OCH 3 , -CH 2 OH, -CH = NOH , pyridinyl, -C≡N and CH = NHOCH 3 The compound according to any one of 1 to 6 or a pharmaceutically acceptable salt thereof. Ｒ３が水素またはメチルである請求項１〜７のいずれか１項に記載の化合物またはその薬学的に許容できる塩。 Compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 7 R 3 is hydrogen or methyl. 前記化合物が、
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（２‐オキソ‐１，３‐オキサゾリジン‐３‐イル）‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐［（４Ｒ）‐４‐メチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐［（５Ｓ）‐５‐メチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐［（５Ｒ）‐５‐メチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐［（４Ｓ）‐４‐メチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐［（４Ｓ）‐４‐エチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１１‐フルオロ‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐［（４Ｒ）‐４‐エチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１１‐フルオロ‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン）；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐［（４Ｒ）‐２‐オキソ‐４‐フェニル‐１，３‐オキサゾリジン‐３‐イル］‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐［（４Ｓ）‐２‐オキソ‐４‐フェニル‐１，３‐オキサゾリジン‐３‐イル］‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐［（４Ｒ）‐４‐ベンジル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１１‐フルオロ‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐［（４Ｓ）‐４‐ベンジル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１１‐フルオロ‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（５，５‐ジメチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐［（５Ｓ）‐５‐エチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１１‐フルオロ‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐［（５Ｒ）‐５‐エチル‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１１‐フルオロ‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（４Ｒ）‐４‐（フルオロメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（４Ｓ）‐４‐（フルオロメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（４Ｓ）‐４‐（メトキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（４Ｒ）‐４‐（メトキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐（（Ｓ）‐５‐（フルオロメチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐クロロ‐８‐［（５Ｓ）‐４‐（メトキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐クロロ‐８‐［（５Ｒ）‐４‐（メトキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（（２Ｒ，４Ｓ，４ａＳ）‐１１‐クロロ‐２，４‐ジメチル‐８‐（（Ｒ）‐５‐メチル‐２‐オキソオキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（４Ｓ，５Ｒ）‐４，５‐ジメチル‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（４Ｒ，５Ｓ）‐４，５‐ジメチル‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（Ｓ）‐４‐アリル‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐（（Ｓ）‐５‐（ヒドロキシメチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐［（４Ｒ‐（テトラヒドロ‐２Ｈ‐ピラン‐４‐イル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐［（４Ｓ‐（テトラヒドロ‐２Ｈ‐ピラン‐４‐イル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐（（Ｓ）‐４‐（３‐ヒドロキシプロピル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐（（Ｓ）‐４‐（３‐フルオロプロピル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐（（Ｓ）‐４‐（２‐ヒドロキシエチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐クロロ‐８‐（（Ｓ）‐５‐（フルオロメチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐クロロ‐８‐（（Ｓ）‐４‐（３‐ヒドロキシプロピル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐クロロ‐８‐（（Ｓ）‐４‐（３‐フルオロプロピル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（５Ｓ）‐４‐（メトキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（５Ｒ）‐４‐（メトキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（５Ｒ）‐５‐（ヒドロキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（５Ｒ）‐５‐（フルオロメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｓ）‐２‐オキソ‐４‐ビニルオキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐｛（５Ｒ）‐５‐［（ヒドロキシイミノ）メチル］‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル｝‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（４Ｓ）‐３‐［（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐２’，４’，６’‐トリオキソ‐１，１’，２，３’，４，４’，４ａ，６’‐オクタヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐８‐イル］‐２‐オキソ‐１，３‐オキサゾリジン‐４‐カルボニトリル；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐｛（４Ｓ）‐４‐［（メトキシイミノ）メチル］‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル｝‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐｛（５Ｒ）‐５‐（メトキシイミノ）メチル］‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル｝‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｒ）‐４‐（（メチルチオ）メチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｒ）‐４‐（（メチルスルホニル）メチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（Ｒ）‐４‐（アジドメチル）‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（Ｓ）‐４‐（アジドメチル）‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐［（４Ｓ）‐４‐（エトキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐１１‐フルオロ‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐｛（４Ｓ）‐４‐［（２‐メトキシエトキシ）メチル］‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル｝‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（Ｒ）‐４‐（ジフルオロメチル）‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（Ｓ）‐４‐シクロプロピル‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｒ）‐２‐オキソ‐５‐（ピリジン‐２‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｓ）‐２‐オキソ‐５‐（ピリジン‐２‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｒ）‐２‐オキソ‐４‐（ピリジン‐２‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｓ）‐２‐オキソ‐４‐（ピリジン‐２‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｒ）‐２‐オキソ‐４‐（ピリジン‐４‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｓ）‐２‐オキソ‐４‐（ピリジン‐４‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐（（Ｒ）‐４‐（（Ｒ）‐１‐メトキシエチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐（（Ｒ）‐４‐（（Ｓ）‐１‐メトキシエチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｒ）‐２‐オキソ‐４‐（ピラジン‐２‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｓ）‐２‐オキソ‐４‐（ピラジン‐２‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｒ）‐２‐オキソ‐４‐（ピリミジン‐２‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｓ）‐２‐オキソ‐４‐（ピリミジン‐２‐イル）オキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（Ｓ）‐４‐エチニル‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐クロロ‐２，４‐ジメチル‐８‐（（Ｓ）‐４‐メチル‐２‐オキソオキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐［（４Ｓ）‐４‐（メトキシメチル）‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル］‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｓ）‐４‐（１‐メチル‐１Ｈ‐１，２，４‐トリアゾール‐５‐イル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐８‐（（Ｒ）‐４‐（１‐メチル‐１Ｈ‐１，２，４‐トリアゾール‐５‐イル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐（（Ｒ）‐４‐（（Ｓ）‐１‐ヒドロキシエチル）‐２‐オキソオキサゾリジン‐３‐イル）‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
｛（４Ｓ）‐３‐［（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐２’，４’，６’‐トリオキソ‐１，１’，２，３’，４，４’，４ａ，６’‐オクタヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐８‐イル］‐２‐オキソ‐１，３‐オキサゾリジン‐４‐イル｝アセトニトリル；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（Ｒ）‐４‐（（Ｒ）‐１，２‐ジヒドロキシエチル）‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐８‐（（Ｒ）‐４‐（（Ｓ）‐１，２‐ジヒドロキシエチル）‐２‐オキソオキサゾリジン‐３‐イル）‐１１‐フルオロ‐２，４‐ジメチル‐２，４，４ａ，６‐テトラヒドロ‐１Ｈ，１’Ｈ‐スピロ［イソオキサゾロ［４，５‐ｇ］［１，４］オキサジノ［４，３‐ａ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（３’Ｈ）‐トリオン；
（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐８‐｛（４Ｓ）‐４‐［（ヒドロキシイミノ）メチル］‐２‐オキソ‐１，３‐オキサゾリジン‐３‐イル｝‐２，４‐ジメチル‐１，２，４，４ａ‐テトラヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐２’，４’，６’（１’Ｈ，３’Ｈ）‐トリオン；
（５Ｒ）‐３‐［（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐２’，４’，６’‐トリオキソ‐１，１’，２，３’，４，４’，４ａ，６’‐オクタヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐８‐イル］‐２‐オキソ‐１，３‐オキサゾリジン‐５‐カルボニトリル；及び
（５Ｓ）‐３‐［（２Ｒ，４Ｓ，４ａＳ）‐１１‐フルオロ‐２，４‐ジメチル‐２’，４’，６’‐トリオキソ‐１，１’，２，３’，４，４’，４ａ，６’‐オクタヒドロ‐２’Ｈ，６Ｈ‐スピロ［１，４‐オキサジノ［４，３‐ａ］［１，２］オキサゾロ［４，５‐ｇ］キノリン‐５，５’‐ピリミジン］‐８‐イル］‐２‐オキソ‐１，３‐オキサゾリジン‐５‐カルボニトリル
からなる群より選択される請求項１〜８のいずれか１項に記載の化合物またはその薬学的に許容できる塩。   The compound is
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8- (2-oxo-1,3-oxazolidine-3-yl) -1,2,4,4a-tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1 ′ H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-[(4R) -4-methyl-2-oxo-1,3-oxazolidine-3-yl] -1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-[(5S) -5-methyl-2-oxo-1,3-oxazolidine-3-yl] -1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-[(5R) -5-methyl-2-oxo-1,3-oxazolidine-3-yl] -1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-[(4S) -4-methyl-2-oxo-1,3-oxazolidine-3-yl] -1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -8-[(4S) -4-Ethyl-2-oxo-1,3-oxazolidine-3-yl] -11-fluoro-2,4-dimethyl-1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -8-[(4R) -4-Ethyl-2-oxo-1,3-oxazolidine-3-yl] -11-fluoro-2,4-dimethyl-1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione);
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-[(4R) -2-oxo-4-phenyl-1,3-oxazolidine-3-yl] -1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-[(4S) -2-oxo-4-phenyl-1,3-oxazolidine-3-yl] -1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -8-[(4R) -4-Benzyl-2-oxo-1,3-oxazolidine-3-yl] -11-fluoro-2,4-dimethyl-1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -8-[(4S) -4-Benzyl-2-oxo-1,3-oxazolidine-3-yl] -11-fluoro-2,4-dimethyl-1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -8- (5,5-Dimethyl-2-oxo-1,3-oxazolidine-3-yl) -11-fluoro-2,4-dimethyl-1,2,4,4a- Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine] -2 ', 4' , 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -8-[(5S) -5-Ethyl-2-oxo-1,3-oxazolidine-3-yl] -11-fluoro-2,4-dimethyl-1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -8-[(5R) -5-Ethyl-2-oxo-1,3-oxazolidine-3-yl] -11-fluoro-2,4-dimethyl-1,2,4 4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-fluoro-8-[(4R) -4- (fluoromethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-[(4S) -4- (fluoromethyl) -2-oxo-1,3-oxazolidin-3-yl] -2,4-dimethyl-1,2, , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-[(4S) -4- (methoxymethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-[(4R) -4- (methoxymethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-((S) -5- (fluoromethyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2,4,4a, 6- Tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ ( 3'H) -trione;
  (2R, 4S, 4aS) -11-chloro-8-[(5S) -4- (methoxymethyl) -2-oxo-1,3-oxazolidin-3-yl] -2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Chloro-8-[(5R) -4- (methoxymethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2, , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  ((2R, 4S, 4aS) -11-chloro-2,4-dimethyl-8-((R) -5-methyl-2-oxooxazolidin-3-yl) -2,4,4a, 6-tetrahydro- 1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3 ′ H) -trione;
  (2R, 4S, 4aS) -8-((4S, 5R) -4,5-dimethyl-2-oxooxazolidin-3-yl) -11-fluoro-2,4-dimethyl-2,4,4a, 6 -Tetrahydro-1H, 1'H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5'-pyrimidine] -2 ', 4', 6 ' (3′H) -trione;
  (2R, 4S, 4aS) -8-((4R, 5S) -4,5-dimethyl-2-oxooxazolidin-3-yl) -11-fluoro-2,4-dimethyl-2,4,4a, 6 -Tetrahydro-1H, 1'H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5'-pyrimidine] -2 ', 4', 6 ' (3′H) -trione;
  (2R, 4S, 4aS) -8-((S) -4-allyl-2-oxooxazolidine-3-yl) -11-fluoro-2,4-dimethyl-2,4,4a, 6-tetrahydro-1H , 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H ) -Trion;
  (2R, 4S, 4aS) -11-Fluoro-8-((S) -5- (hydroxymethyl) -2-oxooxazolidine-3-yl) -2,4-dimethyl-2,4,4a, 6- Tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ ( 3'H) -trione;
  ((2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-[(4R- (tetrahydro-2H-pyran-4-yl) -2-oxo-1,3-oxazolidine-3-yl ] -1,2,4,4a-tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5 '-Pyrimidine] -2', 4 ', 6' (1'H, 3'H) -trione;
  (2R, 4S, 4aS) -11-fluoro-2,4-dimethyl-8-[(4S- (tetrahydro-2H-pyran-4-yl) -2-oxo-1,3-oxazolidine-3-yl] -1,2,4,4a-tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5 ' -Pyrimidine] -2 ', 4', 6 '(1'H, 3'H) -trione;
  (2R, 4S, 4aS) -11-fluoro-8-((S) -4- (3-hydroxypropyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2,4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 '(3'H) -trione;
  (2R, 4S, 4aS) -11-fluoro-8-((S) -4- (3-fluoropropyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2,4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 '(3'H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-((S) -4- (2-hydroxyethyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2,4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 '(3'H) -trione;
  (2R, 4S, 4aS) -11-chloro-8-((S) -5- (fluoromethyl) -2-oxooxazolidine-3-yl) -2,4-dimethyl-2,4,4a, 6- Tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ ( 3'H) -trione;
  (2R, 4S, 4aS) -11-chloro-8-((S) -4- (3-hydroxypropyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2,4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 '(3'H) -trione;
  (2R, 4S, 4aS) -11-chloro-8-((S) -4- (3-fluoropropyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2,4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 '(3'H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-[(5S) -4- (methoxymethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-[(5R) -4- (methoxymethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-[(5R) -5- (hydroxymethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-[(5R) -5- (Fluoromethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2, , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((S) -2-oxo-4-vinyloxazolidin-3-yl) -2,4,4a, 6-tetrahydro-1H , 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H ) -Trion;
  (2R, 4S, 4aS) -11-Fluoro-8-{(5R) -5-[(hydroxyimino) methyl] -2-oxo-1,3-oxazolidine-3-yl} -2,4-dimethyl- 1,2,4,4a-tetrahydro-2′H, 6H-spiro [1,4-oxazino [4,3a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -2 ', 4', 6 '(1'H, 3'H) -trione;
  (4S) -3-[(2R, 4S, 4aS) -11-fluoro-2,4-dimethyl-2 ′, 4 ′, 6′-trioxo-1,1 ′, 2,3 ′, 4,4 ′ , 4a, 6′-octahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -8-yl] -2-oxo-1,3-oxazolidine-4-carbonitrile;
  (2R, 4S, 4aS) -11-Fluoro-8-{(4S) -4-[(methoxyimino) methyl] -2-oxo-1,3-oxazolidine-3-yl} -2,4-dimethyl- 1,2,4,4a-tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'- Pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-{(5R) -5- (methoxyimino) methyl] -2-oxo-1,3-oxazolidin-3-yl} -2,4-dimethyl-1 , 2,4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine ] -2 ', 4', 6 '(1'H, 3'H) -trione;
  (2R, 4S, 4aS) -11-fluoro-2,4-dimethyl-8-((R) -4-((methylthio) methyl) -2-oxooxazolidin-3-yl) -2,4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 '(3'H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((R) -4-((methylsulfonyl) methyl) -2-oxooxazolidin-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -8-((R) -4- (azidomethyl) -2-oxooxazolidine-3-yl) -11-fluoro-2,4-dimethyl-2,4,4a, 6-tetrahydro -1H, 1'H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5'-pyrimidine] -2 ', 4', 6 '(3 'H) -trione;
  (2R, 4S, 4aS) -8-((S) -4- (azidomethyl) -2-oxooxazolidine-3-yl) -11-fluoro-2,4-dimethyl-2,4,4a, 6-tetrahydro -1H, 1'H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5'-pyrimidine] -2 ', 4', 6 '(3 'H) -trione;
  (2R, 4S, 4aS) -8-[(4S) -4- (Ethoxymethyl) -2-oxo-1,3-oxazolidine-3-yl] -11-fluoro-2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-{(4S) -4-[(2-methoxyethoxy) methyl] -2-oxo-1,3-oxazolidine-3-yl} -2,4- Dimethyl-1,2,4,4a-tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5 '-Pyrimidine] -2', 4 ', 6' (1'H, 3'H) -trione;
  (2R, 4S, 4aS) -8-((R) -4- (difluoromethyl) -2-oxooxazolidin-3-yl) -11-fluoro-2,4-dimethyl-2,4,4a, 6- Tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ ( 3'H) -trione;
  (2R, 4S, 4aS) -8-((S) -4-cyclopropyl-2-oxooxazolidin-3-yl) -11-fluoro-2,4-dimethyl-2,4,4a, 6-tetrahydro- 1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3 ′ H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((R) -2-oxo-5- (pyridin-2-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((S) -2-oxo-5- (pyridin-2-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((R) -2-oxo-4- (pyridin-2-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((S) -2-oxo-4- (pyridin-2-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((R) -2-oxo-4- (pyridin-4-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((S) -2-oxo-4- (pyridin-4-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-((R) -4-((R) -1-methoxyethyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2 4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-((R) -4-((S) -1-methoxyethyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2 4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((R) -2-oxo-4- (pyrazin-2-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((S) -2-oxo-4- (pyrazin-2-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((R) -2-oxo-4- (pyrimidin-2-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((S) -2-oxo-4- (pyrimidin-2-yl) oxazolidine-3-yl) -2,4,4a , 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -8-((S) -4-ethynyl-2-oxooxazolidine-3-yl) -11-fluoro-2,4-dimethyl-2,4,4a, 6-tetrahydro-1H , 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H ) -Trion;
  (2R, 4S, 4aS) -11-chloro-2,4-dimethyl-8-((S) -4-methyl-2-oxooxazolidine-3-yl) -2,4,4a, 6-tetrahydro-1H , 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H ) -Trion;
  (2R, 4S, 4aS) -11-Fluoro-8-[(4S) -4- (methoxymethyl) -2-oxo-1,3-oxazolidine-3-yl] -2,4-dimethyl-1,2 , 4,4a-Tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine]- 2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((S) -4- (1-methyl-1H-1,2,4-triazol-5-yl) -2-oxo Oxazolidin-3-yl) -2,4,4a, 6-tetrahydro-1H, 1'H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5 5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-2,4-dimethyl-8-((R) -4- (1-methyl-1H-1,2,4-triazol-5-yl) -2-oxo Oxazolidin-3-yl) -2,4,4a, 6-tetrahydro-1H, 1'H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5 5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-((R) -4-((S) -1-hydroxyethyl) -2-oxooxazolidin-3-yl) -2,4-dimethyl-2 4,4a, 6-tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ′, 4 ′, 6 ′ (3′H) -trione;
  {(4S) -3-[(2R, 4S, 4aS) -11-fluoro-2,4-dimethyl-2 ′, 4 ′, 6′-trioxo-1,1 ′, 2,3 ′, 4,4 ', 4a, 6'-Octahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'-pyrimidine ] -8-yl] -2-oxo-1,3-oxazolidine-4-yl} acetonitrile;
  (2R, 4S, 4aS) -8-((R) -4-((R) -1,2-dihydroxyethyl) -2-oxooxazolidin-3-yl) -11-fluoro-2,4-dimethyl- 2,4,4a, 6-Tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ', 4', 6 '(3'H) -trione;
  (2R, 4S, 4aS) -8-((R) -4-((S) -1,2-dihydroxyethyl) -2-oxooxazolidin-3-yl) -11-fluoro-2,4-dimethyl- 2,4,4a, 6-Tetrahydro-1H, 1′H-spiro [isoxazolo [4,5-g] [1,4] oxazino [4,3-a] quinoline-5,5′-pyrimidine] -2 ', 4', 6 '(3'H) -trione;
  (2R, 4S, 4aS) -11-Fluoro-8-{(4S) -4-[(hydroxyimino) methyl] -2-oxo-1,3-oxazolidin-3-yl} -2,4-dimethyl- 1,2,4,4a-tetrahydro-2'H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5'- Pyrimidine] -2 ′, 4 ′, 6 ′ (1′H, 3′H) -trione;
  (5R) -3-[(2R, 4S, 4aS) -11-fluoro-2,4-dimethyl-2 ′, 4 ′, 6′-trioxo-1,1 ′, 2,3 ′, 4,4 ′ , 4a, 6′-octahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -8-yl] -2-oxo-1,3-oxazolidine-5-carbonitrile; and
  (5S) -3-[(2R, 4S, 4aS) -11-fluoro-2,4-dimethyl-2 ′, 4 ′, 6′-trioxo-1,1 ′, 2,3 ′, 4,4 ′ , 4a, 6′-octahydro-2′H, 6H-spiro [1,4-oxazino [4,3-a] [1,2] oxazolo [4,5-g] quinoline-5,5′-pyrimidine] -8-yl] -2-oxo-1,3-oxazolidine-5-carbonitrile
The compound according to any one of claims 1 to 8, or a pharmaceutically acceptable salt thereof, selected from the group consisting of: 化合物が以下の構造式：The compound has the following structural formula:
Figure 2016506922
Figure 2016506922
 で表される、請求項１〜８のいずれか１項に記載の化合物、またはその薬学的に許容できる塩。The compound of any one of Claims 1-8 represented by these, or its pharmaceutically acceptable salt. 請求項１〜１０のいずれか１項に記載の化合物またはその薬学的に許容できる塩、及び薬学的に許容できる賦形剤または希釈剤を含む医薬組成物。 A pharmaceutical composition comprising the compound according to any one of claims 1 to 10 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient or diluent. 請求項１〜１０のいずれか１項に記載の化合物またはその薬学的に許容できる塩を含有する、細菌感染症治療用または細菌のＤＮＡジャイレース阻害用の、医薬組成物。 A compound according to any one of claims 1 to 10 or containing a pharmaceutically acceptable salt thereof, for treating bacterial infections or for bacterial DNA gyrase for inhibiting pharmaceutical compositions. 淋菌、黄色ブドウ球菌、肺炎球菌、化膿性連鎖球菌、ストレプトコッカス・アガラクチア、ブドウ球菌、凝固酵素（コアグラーゼ）陰性ブドウ球菌、インフルエンザ菌、レジオネラ・ニューモフィラ、またはバークホルデリア属菌種により細菌感染症が引き起こされる、請求項１２に記載の組成物。Bacterial infections caused by Neisseria gonorrhoeae, Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes, Streptococcus agalactia, Staphylococcus, Coagulase-negative staphylococci, Haemophilus influenzae, Legionella pneumophila, or Burkholderia species 13. The composition of claim 12, wherein the composition is caused.
JP2015554245A 2013-01-23 2014-01-22 Compounds and methods for treating bacterial infections Active JP6285960B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361755537P 2013-01-23 2013-01-23
US61/755,537 2013-01-23
US201361859910P 2013-07-30 2013-07-30
US61/859,910 2013-07-30
PCT/GB2014/050164 WO2014114929A1 (en) 2013-01-23 2014-01-22 Compounds and methods for treating bacterial infections

Publications (3)

Publication Number Publication Date
JP2016506922A JP2016506922A (en) 2016-03-07
JP2016506922A5 true JP2016506922A5 (en) 2017-02-23
JP6285960B2 JP6285960B2 (en) 2018-02-28

Family

ID=50033593

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2015554245A Active JP6285960B2 (en) 2013-01-23 2014-01-22 Compounds and methods for treating bacterial infections

Country Status (31)

Country Link
US (4) US8889671B2 (en)
EP (1) EP2948461B1 (en)
JP (1) JP6285960B2 (en)
KR (1) KR102149567B1 (en)
CN (1) CN105229012B (en)
AR (1) AR094565A1 (en)
AU (1) AU2014208965B2 (en)
BR (1) BR112015017519B1 (en)
CA (1) CA2897887C (en)
CY (1) CY1122805T1 (en)
DK (1) DK2948461T3 (en)
EA (1) EA026901B1 (en)
ES (1) ES2780824T3 (en)
HK (1) HK1218293A1 (en)
HR (1) HRP20200401T1 (en)
HU (1) HUE048990T2 (en)
IL (1) IL239860A0 (en)
LT (1) LT2948461T (en)
ME (1) ME03676B (en)
MX (1) MX360650B (en)
MY (1) MY192765A (en)
NZ (1) NZ710091A (en)
PH (1) PH12015501588B1 (en)
PL (1) PL2948461T3 (en)
PT (1) PT2948461T (en)
RS (1) RS60078B1 (en)
SG (1) SG11201505462YA (en)
SI (1) SI2948461T1 (en)
TW (1) TWI603973B (en)
UY (1) UY35274A (en)
WO (1) WO2014114929A1 (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9040528B2 (en) * 2008-10-14 2015-05-26 Astrazeneca Ab Chemical compounds 542
US8889671B2 (en) * 2013-01-23 2014-11-18 Astrazeneca Ab Compounds and methods for treating bacterial infections
MX365261B (en) * 2014-05-29 2019-05-27 Entasis Therapeutics Ltd Fused, spirocyclic heteroaromatic compounds for the treatment of bacterial infections.
CN108136211A (en) * 2015-10-29 2018-06-08 马里兰大学派克分院 For inhibiting the composition of the bacterium infection in people's endocervix and method
CN106632298B (en) * 2015-11-03 2021-06-01 上海科胜药物研发有限公司 Preparation method and intermediate of tedizolid
BR112019024950A2 (en) 2017-06-01 2020-06-23 Bristol-Myers Squibb Company COMPOUNDS CONTAINING REPLACED NITROGEN
CN109111466B (en) * 2017-06-22 2022-08-02 中国科学院上海药物研究所 Benzisoxazole spiropyrimidine triones compound, preparation method and application thereof
CN109111465B (en) * 2017-06-22 2021-01-12 中国科学院上海药物研究所 Thiazolidone spiropyrimidine trione compound and preparation method and application thereof
WO2018233670A1 (en) * 2017-06-22 2018-12-27 中国科学院上海药物研究所 Benzoisoxazole spiropyrimidinetrione compound, preparation method therefor and use thereof
CN108060207B (en) * 2017-12-29 2021-10-15 河南科技大学 Minimum bactericidal concentration determination method based on trace natural compounds
US11905286B2 (en) 2018-08-09 2024-02-20 Antabio Sas Diazabicyclooctanones as inhibitors of serine beta-lactamases
CN111559985A (en) * 2020-05-13 2020-08-21 河南科技大学第一附属医院 Oxazolone compound with bactericidal effect and preparation method thereof

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0759570B2 (en) 1986-05-06 1995-06-28 三井東圧化学株式会社 Method for producing 2-oxazolidinones
US7208490B2 (en) 2002-10-07 2007-04-24 Pharmacia & Upjohn Company Llc Tricyclic tetrahydroquinoline antibacterial agents
JP2007502307A (en) 2003-08-15 2007-02-08 アストラゼネカ アクチボラグ Fused heterocycles as inhibitors of glutamate racemase (MURI)
WO2005066119A2 (en) 2003-12-31 2005-07-21 Schering-Plough Ltd. Antibacterial 1-(4-mono-and di-halomethylsulphonylphenyl)-2-acylamino-3-fluoropropanols and preparation thereof
EP1888597A2 (en) 2005-05-09 2008-02-20 Warner-Lambert Company LLC Antibacterial agents
DOP2006000268A (en) 2005-12-22 2007-07-31 Pfizer Prod Inc ANTIBACTERIAL AGENTS
CL2007003332A1 (en) * 2006-11-24 2008-06-20 Actelion Pharmaceuticals Ltd COMPOUNDS DERIVED FROM CONDENSED HETEROCICLES; INTERMEDIARY COMPOUNDS; PHARMACEUTICAL COMPOSITION; AND USE IN THE PREVENTION OR TREATMENT OF BACTERIAL INFECTIONS.
AU2008272693A1 (en) 2007-07-02 2009-01-08 Astrazeneca Ab 3-spiropyrimidinetrione-quinoline derivatives and their use as antibacterial agents
MX2011003598A (en) 2008-10-14 2011-04-27 Astrazeneca Ab Fused, spirocyclic heteroaromatic compounds for the treatment of bacterial infections.
US9040528B2 (en) 2008-10-14 2015-05-26 Astrazeneca Ab Chemical compounds 542
US8952149B2 (en) 2012-09-26 2015-02-10 Zoetis Llc Tricyclic tetrahydroquinoline antibacterial agents
US8889671B2 (en) * 2013-01-23 2014-11-18 Astrazeneca Ab Compounds and methods for treating bacterial infections

Similar Documents

Publication Publication Date Title
JP2016506922A5 (en)
HRP20200401T1 (en) Compounds and methods for treating bacterial infections
ES2244802T3 (en) DERIVATIVES OF OXAZOLIDINONE AND / OR ISOXAZOLINE AS ANTIBACTERIAL AGENTS.
JP2016511258A5 (en)
US7498350B2 (en) Oxazolidinones as antibacterial agents
WO2004078753A1 (en) Hydroxymethyl substituted dihydroisoxazole derivatives useful as antibiotic agents
EP1567532A1 (en) Oxazolidinone and / or isoxazoline derivatives as antibacterial agents
JP2016506962A5 (en)
RU2015101102A (en) Heteroaromatic methyl derivative of cyclic amine
JP2016507551A5 (en)
US20060058314A1 (en) Oxazolidinone derivatives and their use as antibacterial agents
JP2020502230A5 (en)
JP2013523814A5 (en)
JP2017529365A5 (en)
JP2009503021A5 (en)
US20060052399A1 (en) Oxazolidinone derivatives as antibacterial agents
US20060116389A1 (en) Antibacterial oxazolidinones
ZA200504309B (en) Oxazolidinones as antibacterial agents.
JP2016533367A5 (en)
RU2471795C2 (en) 3-amino-6-(1-aminoethyl)tetrahydropyrane derivatives
RU2015144720A (en) TRICYCLIC TRIAZOLE COMPOUNDS
RU2022100544A (en) PYRIDINE CARBAMATES AND THEIR APPLICATION AS MODULATORS OF GLN2B RECEPTORS
RU2020104753A (en) DERIVATIVES OF 2-OXO-1, 3-OXAZOLIDINYLIMIDAZOTHIAZOL
RU2010101003A (en) 3-AMINO-6- (1-AMINOETHYL) TETERAHYDROPYRANE DERIVATIVES